Fortune Doesn't Favor Fools
by Emooly
Summary: Miss Fortune and Gangplank end up meeting at a bar in Bilgewater for a night of drinking and gambling. After Gangplank wins with a trump card, the pair decide to get together and share an unforgettable night of pleasure.


"Hit me," I said, swallowing hard, and shifting uncomfortably in my seat. Damn that blasted Gangplank. My hand was completely useless. It would be pointless to continue betting. But I still did it anyway. You ask why? A mixture of pride, boldness, dare, and well, fun. It was more entertaining than surveying the ocean water. Nowadays invading an enemy ship was never as exciting as it used to be. My crew would rejoice with the treasures and riches we would strike upon, but now it has merely become a tradition. A custom we work and toil over on a daily basis and never genuinely appreciated.

Gangplank looked at me from underneath his cap, that annoying ass smirk plastered over his visage once more. It was as if every single time we agreed to gamble, he always had a trick stashed up his sleeve. One of his fingers danced over the tip of a card.

"So Fortune," he said suddenly. I took a sip of whiskey and returned his attempt at a start of a conversation.

"Yes, Gangplank?" I asked, batting my eyelashes. Maybe I could flirt my way out of this. Probably not. Gangplank had me memorized. A group of pirates have already formed around our table, hooting and laughing. Some were talking amongst each other. Whisper, whisper, whisper. How irritating.

"So if I win," he pronounced slowly, his eyes set on the pile of gold glistening before him. "I get the money."

"Of course, of course," I answered. "You earn what you bet. That has always been the rule." I looked rather bored, inserting a finger into my tangled mess of strawberry hair, twirling a lock around my hand. I quickly brushed it out of my face as soon as I noticed Gangplank's stare. I just wished this banter would end soon. I was getting tired of this.

"Lovely," he replied, taking a shot of vodka from his glass, as he swirled it around. I gazed at the liquid, and silently admired how he could handle such a strong beverage, and is still able to articulate himself. His large hands were clamped securely around the mug, but his eyes remained on mine. He was trying to read me. I could tell. And by the looks of it, he had me all figured out. I was trapped. I could not to anything. He had me wrapped around his finger. "It's your turn to bet, by the way."

"Hmm," I murmured. "Well, you cleaned me out on the money aspect.."

He raised his eyebrow as I stood up, and walked behind him.

"What if we make a little trade?" I suggested, in an obviously fake, high-pitched voice. Gangplank snorted. "I've been feeling so lonely lately," I continued, placing my hands over his shoulders. "And I would really like it if we did something special together."

"Not happening," Gangplank immediately replied, emptying his vodka glass before ordering another one.

"Aw come on, honey," I cooed, making sure my breath tickled his earlobe. "I know you want it." I proceeded to massage his shoulders, and placed my lips at the base of his neck. "Pretty please with a cherry on top?"

"No way," Gangplank replied simplistically. Usually I would have the man hooked by now. They would come panting, desperate for a taste. Licking and lapping up the saliva dripping from their mouths like wild animals. He, however, remained undisturbed by my social tactics.

I pinched a fold of his skin as tightly as I could, which obviously elicited some pain from him. He grunted, but only slightly. I did that purposefully. Served him right for embarrassing me in front of all those people. I walked back to my seat and folded my arms across my chest, pouting angrily. I muttered to myself as Gangplank continued to chuckle at my foolishness. He rubbed his mustache with curiosity, observing my every move.

"Unless that is your offer," Gangplank grumbled suddenly.

"What do you mean?" I asked, leaning in, intrigued by his statement.

"Are you putting your body on the line?" Gangplank questioned curiously. "And all the gold on the table?" I shrugged my shoulders. "Sure, why not?" I giggled, throwing my hands in the air. "I have nothing else to lose."

_Great. Pretend that you have everything under control. Maybe that will lull him into a false sense of security. _

"Interesting," Gangplank commented. I hated him with every fiber of my being. He was always so calculated like that.

"So," I said. "It is your turn."

"Wonderful," Gangplank responded, throwing his cards on the table like he was making a deal. "Royal flush. Can you beat that?"

My eyes widened, glazing over the perfectly glossed cards. He was cheating. He must have been. There was no way. My fingers trembled. I bit my lips nervously as the crowd around us started to converse. What could I possibly do now? He was still staring at me. It was so annoying. Whenever we locked gazes, I would turn away immediately, and then after several moments, I would look back just to check if we was still looking at me. He usually always was, and would smirk at my paranoia. The bastard.

"Aw come on, Gangplank.." I laughed apprehensively. "You did not."

"Oh, but I did," he replied. "Miss Fortune. You really are something."

I licked my lips, and stood up once more, setting my cards face down on the table. I made sure to cross my ankles as I walked, one foot over the other. I swayed my hips, and allowed other male pirates from the spectating scene to have a nice view of my ass. It was definitely not something they could see everyday. This was why I wore my sexiest outfit that day. Just for this occasion. My black and white lace corset squeezed my boobs and pushed them upward, so everyone could see them. My wrists were decorated with frilly sleeves, which were held back by some black elastic bands. My legs were concealed with tight, dark leggings, accentuating my round behind. My long, slender thighs and calves were also bound by the silky fabric of the cloth. I whipped a piece of my hair to one side of my neck, and puckered up as if I was ready for a kiss when I stood before Gangplank. He seemed more interested in his alcohol than he was in me. This upset me tremendously.

"Mmm, baby," I moaned as I managed to seat myself in his lap. I ground my ass into his legs, and made small, circular motions with my buttocks as he turned in another direction. I licked his jawline, making sure to run over it with my warm tongue, resounding cat calls from the crowd of pirates that surrounded us, which were for the majority, drunk, sexually aroused males. Perfect. Exactly the reaction I was looking for. I knew precisely what he liked- having something no one else can get ahold of. Me. And in front of all these pirates he rivaled and despised. "I know we have hard feelings sweetie, but maybe we can work it out later.." I ran my fingertip over his muscled chest that was exposed to the air of the tavern. His white undershirt was unbuttoned so it displayed his strong, capable frame. His arms were also gleaming with sweat, under the dim lighting. The collars of his crimson and gold vest concealed his expression as he pretended to be inspecting something else located in another part of the bar.

"Nope," he replied, not even laying a hand on my body.

"Stop trying to fight it," I whispered seductively. "I know you are only hiding it when you say that you are the only one who can resist my charm. So much of that masculine pride I have been getting from you recently.."

"You lose, Sarah Fortune," he stated. "And that is the end of the line." He took another swig of vodka.

"Oh, but it's just no fun when that happens," I whined childishly, squirming around in his lap. "Come on, please? Just let me go this once."

"Nope," Gangplank replied again. "Just live with the consequences, _baby_." He added the affectionate catchphrase toward the end purposefully, as if to mock me. My eyes narrowed. I could kick him in the balls right now if I wanted to, but I resisted the urge. That would ruin all my chances.

I pressed my breasts against his bare chest, so he could feel and know precisely what he was turning down. "I need you, Gangplank," I purred, taking his free hand and gently playing with his fingers. "I want you.. what would I do when I am broke? Roaming the streets, penniless and alone. No food, water, shelter, home, and worst of all- no you! How am I supposed to live like that?"

Gangplank snorted, ridiculing my statement. He found my acting to be hilarious. I prided myself in that fact. "You get around, Fortune," he stated. "I know that for a fact. All too well." He placed his hands on the back of his head.

"But I can't live without you, sweetie," I attempted. "You are like the air that I breathe. Every second, I burn, I pine, I desire. For you to have me." He was enjoying this. I could tell. One glance at his arrogant, satisfied smirk guaranteed me of that fact. I placed my hand on his face and gazed into his eyes with bloody intent. "So how about it, stud?"

"Hmm, let me think about that.." he placed a finger to his chin. At first, I almost believed he was actually contemplating my offer. "How about.. no?" He laughed uncontrollably as I stood up and kicked him in the shin.

"Douchebag. Asshole. Jerk," I hissed to myself as some of his men came from behind him and gave him high-fives and congratulatory slaps on the back and rounds of applause.

"Sex with Fortune and a whole pouch of money," one bystander mused. "And good taste in liquor. What a lucky man."

I snorted, and crossed my legs. I bet he was quite satisfied with himself. That son of a bitch. I would have my crew pound him to smithereens if that were part of the package deal. After he dealt with numerous congratulations and pats on the shoulder, he stood up from his seat and walked toward me.

"May I buy you a drink?" he offered, trying to hold my stare. His brown eyes sparkled with a slight maroon color amidst the dim lighting.

"A margarita, please," I say without looking at him. "With salt."

"Humph," he snorted. "Wise choice."

_What was he thinking? Is he trying to hit on me? Probably. I mean, look at me._

Several moments passed before he returned with several shot glasses. "My treat," he reminded. I rolled my eyes, and snatched one from the tray.

"Is this another one of your games, Gangplank?" I asked, putting more emphasis on his name.

"You can say that," he responded, still keeping his eye on me, as if he let down his guard, I would just slip through his fingers. "So let me lay down the law here. Let's play a drinking game. If I win, I get to keep all of my previous earnings. That includes the gold, and some nice hot Fortune fuck. And you become my crew's sex slave for the next month."

I rolled my eyes at that phrase. So materialistic. "Seriously?"

"Men get bored on long voyages out at sea," Gangplank explained. "They don't work if their bodies don't get the satisfaction they crave. And you are the perfect little whore for the job."

"And if I win?" I asked, raising my eyebrows, trying to brush off his previous insult, no matter how badly it hurt. I crossed my arms across my chest to conceal my puppies from his lingering gaze.

"I set you free," Gangplank replied. "And you keep the money. Pretty sweet deal, huh?"

"So are we drinking, or what?" I asked.

Gangplank snorted. "What a badass."

I nodded as if to confirm his aforementioned remark, and emptied my glass in one gulp.

"Ohoho, starting strong now are we?" he commented, still swirling around the contents of his drink in the glass.

"It's your turn," I said, completely ignoring his previous statement. I wiped some spilled margarita from my chin and licked my lips, still maintaining my gaze. It was like a staring contest. I wasn't backing down anytime soon.

He gave me an obnoxious smirk, and poured the alcohol down his throat. I did the same. The cycle continued until there were only several glasses left on the tray. I started to feel dizzy. I felt like there was something wriggling around my stomach, tickling it and making me want to upchuck everything I drank earlier. I placed a hand on my forehead as I watched Gangplank from the corner of my eye. An hour has probably passed, and he was still going strong.

_How in the world could one man take in so much liquor? _

"So is that a forfeit, Sarah?" he queried, raising another shot glass of margarita in the air. "You look like you are about to hurl. I wouldn't want you to pass out. So delicate."

"Like hell!" I countered, taking another shot glass from the tray, and draining it of its liquid. In fact, I took another one. Two in a row. There was no way he could still continue this game.

"Feisty, aren't we?" he smiled. But it wasn't anything endearing or kind, I'll give you that. He took three shot glasses, and drank them one by one.

_How._

"My head hurts," I groaned, burying my face into my hands. Everything hurt. My heart pounded against my chest. I felt as if it was about to explode. Alcohol always made me feel this way. I held my stomach with another hand once I looked up to see Gangplank ordering another platter.

_Is he insane?_

My blood pounded against my eyes as I rubbed my temples with my fingertips.

"Mmph," I groaned. This was not going in my direction. Not at all.

"Why are you giving up so soon?" he questioned. "I am just getting started."

I moaned in response. "Everywhere hurts.." I complained, laying my head down on the table. Gangplank continued to take more shots. Once he saw me in defeat, he crushed the shot glass into his hands, and stepped toward me.

"I win," he said, lowering his voice to my ear. I could not remember anything after that, since I blacked out.

I could not see. I was blindfolded. Or at least, I think I was. I could not even touch my face. My wrists were handcuffed behind my back. I would scream for help, but a ball gag was fitted in my mouth and if I attempted on creating a noise, it would only sound more like a pathetic whimper than a noticeable cry. Just fantastic.

_Fuck. What have I gotten myself into this time. _

My most recent memory was a poker tournament at some tavern in Bilgewater. Let's just say I got really drunk. It was a stressful week out at sea, and I got reckless. Like I usually do. Whatever. So anyway. One thing lead to another and I started to put more than money on the line. To say the least. I struggled with my restraints. I was stripped of my usual clothes. Speaking of which, where were they? I was completely topless other than my breasts, which were held tightly in some push-up bra of the sort. Something tight, and elastic. It was uncomfortable. I did not like the feeling. I felt a skirt swish over my ass cheeks as I tried my move around. What were they doing, putting me in this slutty outfit. I felt heels click on the soles of my feet as well.

_Shit. My ankles are tied together with ropes too. _

I continue to squirm around in my constraints. There has to be a way. If I could untangle myself from the ropes on my feet, maybe I can fiddle with locks on my handcuffs and get the fuck out of here.

"Well well well."

I heard the voice echoing from a corner of the room. I turned my head apprehensively. It was deep, low, husky. It sounded so familiar.

"Mmph!" I screeched, but my scream was muffled by the ball gag."Mmmm!"

I felt a hand close over my shoulders. I jumped at the sudden touch. "My little Sarah Fortune," the voice whispered. I immediately acknowledged that it belonged to Gangplank. "So sexy when you are all tied up like that.. so helpless and lonely." I felt him untie my blindfold. Thank God.

Gangplank was dressed like he was back at the tavern, his muscled chest and arms exposed, but his abdomen still concealed by his white undershirt. His gold and scarlet vest was pulled over his torso, and flowed down to his knees. His legs were covered by leathery trousers, and his feet were tucked snugly into some boots. His hat still sat proudly on his hat, which he removed and placed on mine instead. I did not like that gesture.

"What to do, what to do," he murmured to himself. "We are all alone, after all. I get to keep you all to myself for one night so I can do whatever I want with you. But where to start.." I realized we were sitting in his bedroom. He owned probably one of the largest estates in all of Bilgewater, plundering treasure islands, ransacking enemy ships to build his empire of wealth, alcohol, and prostitutes. He was one yummy pirate I would love to sink my claws into if I had the chance. But he was perfectly aware of my trickery. He knew I was a gold-digger. The bastard. "How about you give daddy here a lap dance?" He pulled out a wooden chair. I stared at it, and then shook my head violently. No way in hell.

"It was not a question, Fortune," Gangplank spoke slowly. "Do it now or there will be punishment later." I remained adamant. I would call him a million things right now if only the ball gag were out of my mouth. I still refused. Anything would be better than giving a lap dance to that motherfucker.

"It's your choice," he replied. "Down on all fours."

I don't listen. I am not going to be subject to these antics. I am Sarah Fortune. Not a sex slave.

I shake my head and pretend to look off into another direction.

"Down on all fours," Gangplank repeated, his voice now dangerous. "Don't make me force you. I wouldn't want to use this." He picked up a whip, which was lying conveniently at his feet, and slapped the ground menacingly with it. "Now."

I quickly obliged. Okay, he had me there. Whips hurt. Like hell. No way I was letting one anywhere near me. Especially my flawless skin. No thank you. I made sure my ass was facing skyward, and I allowed my palms and knees to kiss the ground. He stood from behind me, and knelt down, dropping the whip. It was as if he was expecting my ass. What the fuck was he doing down there? He better not pull anything weird. I felt a slap against my butt cheeks. I released an uncharacteristic squeal, and immediately bit my tongue.

"You like that?" he asked, slapping my ass once more. Was he giving me a spanking session for rebelling against him? "That's what you get for disobeying your master, Fortune." His hits started off gentle, but then became increasingly hard. Even for me. It began with several taps. I figured, sure why not? It might actually be kind of hot. But then it started to hurt.

"Mmm," I moaned, shaking my head as his hand flew to my ass cheeks. I looked behind me to see him spanking me to oblivion.

"One more and then the whips start coming in," he threatened. "Don't make me use it. I don't want to do this to you."

_Aww, how sweet. He was being considerate for once. Bullshit. I didn't buy it. _

I remained stubborn. I was not giving him a lap dance. Not in a million years. I was perky, sure. But no way in hell was I a stripper. No sir.

Okay, I will admit it. The pain stung. It left red, blotchy marks all over my ass. His hands were large, and he was relentless when it came to spanking. After several more smacks, he started to whip me. Hard. He started by lashing it onto my back. I squeaked. But I was not begging for mercy. "At your limit yet, Fortune?" he asked before sending another streak over my butt. I shook my head violently. Not even close. Keep going. I dare you. "Do you want me to do this the hard way?" He continued his molestation of my ass, spanking it continuously, alternating between his hands and the whip. I wondered what he meant by that. Gangplank grabbed me by the hair and pulled me upward, and proceeded to spank me over the butt and back. He then allowed my face to come crashing to the ground. My wrists were still handcuffed behind my back. My body felt sore, almost violated as I laid face down. Everywhere hurt. My head was pounding. I felt some blood trickling from the corner of my lips. I felt defenseless- completely vulnerable to him. I could not do anything to stop it. I threw myself into this mess, so I have to face the consequences with honor. Even if every shred of my dignity is torn away from my hands. I heard Gangplank walk to another location of the room, probably to take out some other horrible sex device to use on me. I clenched my body once I heard him step back toward me. What was he going to do to me? I suddenly felt scared. Afraid. I had to last the night. Even if it killed me to do it.

His hands entered my hair once more, and pulled me up. I was still on all fours, and my body was completely exhausted. Gangplank's fingers proceeded to wiggle into my push-up bra, and flicked out the carnation nipples of my tits. I felt something chilly press up against my breasts. No, it was icy. Warm. Hot. I jumped, desperately squirming away from him. Saliva dribbled from my mouth as the ball gag was still squeezed tightly between my lips. It dripped in between my boobs, which only irritated the burn even more. Gangplank held a steaming poker stick in one hand, and a burning candle in the other. He squeezed some wax from it, and allowed it to spill all over my toned stomach, thighs, and calves. A squeak managed to escape my lips. He was kind enough to remove the ball gag from my mouth, allowing it to dangle menacingly over my neck. I took a deep breath, and moaned from all the pain around my body. From the oozing pain of the candle wax and the burn of the poker stick to the sting of the whips and the ache from the spanks, I could have fallen unconscious right then and there. Until he inserted his fingers into my mouth.

"So, how about the lap dance?" Gangplank cooed softly, allowing his index and middle finger to scrape over my teeth. "Or I will continue burning you."

I still shook my head. "I am not giving in that easily," I replied, once he removed his hand from my mouth. It felt amazing to talk again.

"Suit yourself," he responded. He took the poker stick and began to press circles around my breasts. My beautiful skin. The one that I apply lotion on every morning. It's all ruined. Thanks to this bastard. I will probably have these burns for at least several weeks.

"Ouch!" I whined, pulling back from him. His hand was pressed firmly against my back, preventing me from accessing any of my escape routes. He proceeded to knead my tits, allowing the burns to touch one another. They stung insanely. I practically yelped in response to the feeling. And I could not do anything about it because my wrists were still handcuffed.

"So big," he chuckled, playing with them with his fingers. Squeezing. Fingering. Rolling. Flattening. "Are they even real? They don't seem to fit your tiny frame."

I would have slapped him. "Shut the fuck up!" I snapped, and moaned once he twisted my nipples horizontally. "Ahh!" As my mouth opened, he inserted three fingers into it so I would stop talking.

"Shhh," he whispered. "You still have one more chance before the grand finale. I will give you an opportunity to give in."

"No way in hell," I grunted through gritted teeth. And with that, I felt the greatest pain in my life. The poker stick was pressed up against my nipple.

"OH!" I screamed, head lurching backward. Gangplank was ruthless. "Fine!" I gave in. It hurt so badly. I had to. He pulled up my lacy bra and spanked my ass, standing up to take his seat in the wooden chair he pulled out earlier. He helped me to my feet, and then pushed me firmly against the stony wall of his bedchamber.

"I thought you would see it my way, Fortune," he said, smiling back at me. "You would look so sexy in the outfit I have prepared for you."

"What?" I queried, turning around. "Those skimpy skank suits you decorate your slave girls with? No thank you."

"Oh, but you are missing one important detail," Gangplank countered, as he caught me from behind, squeezing my hips roughly. I squealed. "You are my sex slave now." He whispered that statement huskily into my ear.

"So maybe you can wear this for me?" he asked, purposefully scraping the uncomfortable, lacy fabric of a lingerie costume over my stomach. "I wouldn't want to go back to spanking and whipping and burning you again. You won't like that either, would you?"

"Can I at least have a private space to change?" I questioned. Gangplank laughed as if I was joking. Well, that's my answer. "Let me get that skirt off you."

"Huh?" I turned around to see him sliding it over my long, slender legs, and tossing it into the corner of the room. He slid a finger into the fabric of my thong, stretched, and allowed it to slap back against my skin.

"Mmm!" I moaned. It hurt. Really badly. Especially since my ass was already covered with whip marks and bruises. I suddenly felt an urge for him to touch my pussy. Creams and juices proceeded to slide out of my hole, and down my inner thigh. I tried to cross my legs to prevent him from seeing, but he noticed almost immediately.

"Getting horny, now are we?" he chuckled, allowing his finger to run over the river of liquid that has begun to coat over my legs in a layer of shimmery fluid. He tasted it, and smacked his lips together. "Better than vodka, that's for sure."

I blushed. Such a stupid compliment. But I somehow felt warmed by it. How pathetic of me. He inserted his fingers into the straps of my bra, and pulled, snapping it backward. He then undid the hooks, immediately grasping my breasts with his hands.

"Hah!" I wanted to fight back the moan. I really truly tried. But it spills from my lips. "Ahh!" It felt so good to have him fondle my boobs like that. No one has done that for quite some time. And the best part was that he knew exactly how I liked it. Which nipple was more sensitive than the other, where I liked to be kissed and where I didn't, and exactly where my G-spot was located, where he can ram and pound and hit over and over again with his cock and I would still want more.

"My, my," Gangplank murmured. "They are so.. supple." He bit a nipple in between his teeth, and pulled it outward, allowing it to snap back into place. I whimpered at the gesture.

"Stop it!" I squealed. "It hurts."

"As if I would listen to what you have to say," Gangplank smirked. He wrapped an even more tight, lacy push-up bra over my tits. It was creamy white in color, and almost constrained my boobs from pouring outward. He then reached from around my back and tied on a small, short-sleeved cardigan that resembled a schoolgirl outfit. It made my cleavage pop out all the more as he added one more final knot to the cloth. Just as I was about to moan once more, he slipped on a plaid skirt over my hips, and tightened its belt with his fingers.

"Thank you for dressing me up," I said, as intoxicatingly as possible as I stepped away from him. Immediately, Gangplank wrapped his arms around my stomach and held me against his torso.

"I am not finished yet, princess," he replied. He roughly placed a collar over my neck, and tightened it. It became even more difficult to breathe with the frilly bra and corset around my chest and the strip of leather around my throat. He then, with an uncharacteristic gentleness, allowed me to step into a pair of translucent knee socks with lace at the top. I hated how the fabric tickled the bottoms of my feet. He then strapped on some high heels over my socks, and adjusted his hat over my head. "Perfect," he said, while hooking a leash onto my collar and pulling me toward him. "Now give daddy the lap dance he deserves."

I batted my eyelashes at Gangplank one last time. "But I don't want to do it," I whined. "Do I really have to?" I allowed my bottom lip to pour out, resembling a vulnerable puppy. "Please?"

"Shut the fuck up and sit on my lap, you slutty bitch," Gangplank ordered. "You shall address me as 'master,' and if you do not do exactly as I say, I will whip you, spank you, and then burn you with the candle and the poker stick. Now we wouldn't want that, would we?"

I shook my head, clasping my hands over my chest. "Okay," I whispered, completely surrendering to him this time. He released his grip on my leash and sat down in the wooden chair. I took several steps back. _Let's see, how do we do this again. I remember one time when I was really drunk and decided to go into a gentlemen's club and strip for all the pirates at the local tavern. This shouldn't be any different. _

I made sure to sway my hips, and to bite my lips slightly, looking horny and sexy. I tossed my hair back over my shoulder and placed a finger in between my lips. Looking all naughty and flustered like that. I am sure he loved it. My eyes glazed over his rock hard cock, which was already bulging menacingly from the tightness of his jean trousers. I wanted to suckle on it so badly, to have it stretch open my mouth and make me gag like the dirty girl I was. I turned around for him, allowing him to receive a full view of my ass before slamming it down onto his bulge, rolling it around and pressing downward so he could feel the round of my butt suppressing his boner. I began twisting in a rhythmic motion, making circular shapes around his crotch and allowing him to grip onto my supple ass cheeks for security.

"That the best you can do, Sarah?" he mocked teasingly, kneading my butt with his rough, calloused fingers.

I snorted. "Just you wait and see, master," I countered quickly, emphasizing the last word with sheer naughtiness. This caused him to raise an eyebrow, which elicited an adventurous giggle from me.

I decided to turn back around so that I was facing him, and sat in his lap, wrapping my hands behind his neck and allowing my pussy juices to spill over his pants, gently wetting his already aroused cock.

"Mmmm," I moaned, rubbing circles around the bump, biting my lip and flicking a piece of hair behind my shoulder. I felt his hands slide up my toned stomach, holding me into place so that I would not finish before he wanted me to stop. So selfish. I tried to tease him, moving away from his cock by lifting my pussy over, allowing the cold air to lick its edges, before having him slam me back into his lap once more, tightening his control over my playful game. I then took his head and allowed his yummy, prickly face to nestle over my smooth, warm tits.

"You like that, big boy?" I asked, grabbing his head by the ears and allowing his shaven beard to tickle over my soft, supple boobs. "You like it when I do this, hm?"

This must have angered him, because he probably perceived it as me talking down to him. He immediately suppressed my teasing, sarcastic tone by biting down hard on the inner side of my tit.

"AH!" I squealed, jumping at the feel of his teeth gnashing viciously against my flesh. His hot tongue soon escaped from the prison of his lips, licking his way between the valley of my cleavage and making me see stars. It felt like warm, hot jelly was sliding between my most sensitive spots, and stimulating and tickling my skin over and over again.

"You like that, my little princess?" he asked between licks, his voice muffled by my breasts. "Mmm, so tasty. You will always be my favorite flavor, Fortune." This statement sent shivers up my spine, as I suddenly lost myself in a daze, spacing out in the midst of his hard tongue rolling over the skin of my breasts, slightly tickling the outskirts of my nipples, but never fully engulfing. He knew that action would drive me over the edge. His molesting of my breasts soon became more violent, as his hands came into play, gripping each side and forcefully kneading and groping. He then proceeded to shove my tits into his mouth, licking each one like a popsicle, sucking generously onto the nipples. As I felt the hot caves of his mouth press over them, I immediately began to moan and scream in response to the caressing motion.

"So good.." I whimpered, subjecting to his sweet surrender. "Mmmm." He yanked my leash slightly harder in response to that verbal statement, continuing to violate my breasts with his sucks and licks. His large hands were clamping my thighs down into his lap, as his mouth resumed to work its magic upon my bosom.

"How about a change of pace, Fortune?" he suggested, in between licks, trying to lock his gaze with mine.

"Try me," I challenged fiercely, giving him a seductive wink. Immediately, Gangplank grabbed my ass cheeks and lifted me off of the chair, my leash dangling over the ground below.

"Ahh!" I moaned in response, wrapping my thighs instinctively around his waist. I hugged his face close into my boobs, enjoying the feeling of his stubble rubbing against my tits. Gangplank then proceeded to throw me onto his crimson bed, his hands running greedily over my delicious curves. I gripped the bedsheets below me for dear life, the rough fabric tickling against my soft, supple skin. This action completely exposed my chest to Gangplank's view. He then buried his face back into my boobs as I screamed out, loving it more after each second chimed on. This foreplay continued for half an hour or so, consisting of me moaning and screaming, my legs still wrapped around Gangplank's waist. After breaking away from my nipples, he proceeded to remove his clothing.

"What are you doing?!" I cried in protest. "Don't stop."

"I am just getting started," he replied, after ripping his shirt over his head and slipping his tongue into my mouth. We made out for several minutes. The kisses were light and playful at first but then became ever more dark and passionate. His hands began to travel through my luscious, ruby locks.

"I've always loved your hair," he murmured softly. "So red and bright and.." He paused in between our kissing session and took a long, hard smell.

"Do you scent this?" he asked suddenly, his brown eyes interlocking with mine, his brow suddenly furrowed with concern.

I shook my head, caught off guard by this random question.

"It smells.. heavenly," he commented. "I love everything about the way you smell."

I didn't really know how to respond to that. I just sat there, flushed. He liked the way I smelled? How weird and completely bizarre was that.

"J-just.." I blushed, flushing the same color as my tresses. I fiddled with the frilly fabric of my knee socks for a second, as Gangplank continued to watch me, trying to see if I will release a reaction. "Just shut up.. and kiss me."

He completely obliged after that. I think we can both agree on not making cringeworthy, platonic statements. I mean after all, he was Gangplank and I was Miss Fortune. I ran my hands over his strong, hard biceps as the kissing intensified and now my entire back was pressed against the fabric of his bedsheets. His tongue flicked against mine, as the suction between our lips became increasingly passionate.

"Mmph," I cried, as he broke away once more, reaching toward a nearby nightstand and removing a bottle of massage oil from the drawer beneath.

"Want to get messy?" he offered with a sexy smirk.

"Surprise me," I replied.

He cupped his hand and poured in a generous puddle of the liquid.

"Turn over," he commanded.

"Mmm.. okay," I obliged, unwillingly of course- but I was curious to see what he had up his sleeve. It wasn't everyday that the great Gangplank had yet another bright idea of his.

My breasts were pressed up against the crimson fabric of his bedspread, my back and ass cheeks completely exposed to his touch. I was surprised by the feeling of his rough, calloused hands massaging my skin with the utmost gentleness. A sticky residue was clinging onto his skin and then spreading onto mine. It felt absolutely wonderful.

"Ahhh!" a moan escaped from my lips. "Mmm.."

"You like that?" he asked. He was kneading the small of my back, rolling into the two dimples right above my ass cheeks. He continued to rub and knead, making me tingle all over from his amazing touch.

"Your hands.." I commented between another groan. "They are so.. ahhh!"

I was surprised by his full lips kissing into one of my back dimples, alternating between each one. It was such an unusual, satisfying feeling. A place that never received much affection on my body was now being tortured beyond words. It just felt way too good. He was starting to use his knuckles now, pressing them into the middle of my back, after he kneaded it for several minutes, adding another dollop of body oil as needed. He then proceeded to work his way up to my neck, squeezing the back of it and then rubbing it into the rounds of my shoulders. He then drizzled some of the liquid in between my shoulder blades, massaging it into my skin and making me see stars. His hands worked some sort of magic against my body; they just felt so connected and perfect and well, right. After massaging the oils into the flesh on my back, he started to caress his way to the sides of my breasts.

"Mmm," I moaned.

"You like that?" he asked, lowering his chin so that his lips leveled to my ear.

I nodded reluctantly. "J-just keep doing what you are doing.." I requested.

"As you wish," he replied.

His fingers returned to my breasts. He seemed to be mesmerized by the round, squishy mounds. He squeezed them with such force, and then released, returning back to his rhythmic movement.

"Let's see if I remember which one is more sensitive than the other.." he murmured to himself. "Last time we did this was so long ago, I may as well have forgotten."

"Try me," I countered intuitively. He then nestled his stubbly chin in between each one, his hands still on top of my boobs.

He traced his fingertip so that it rested comfortably on top of my left nipple. Electricity erupted in my nether region, as my back arched toward him, pressing my body against his hands. He wiggled his fingertip so that my nipple followed it, almost as if it was guiding which direction it should face. My breasts immediately hardened at this gesture, as another gasp escaped from my mouth. He then lowered his lips so they grazed my breast, and then bit down. Hard.

"Mmmmph!" I groaned, my voice more high-pitched and feminine-sounding than usual. I hated how he did that to me, the way he read my mind and body language like a book. My legs twisted and naturally folded on top of each other as I pulled my body to the left side.

"Hard already, huh?" he commented, slapping my left breast playfully and proceeding to molest it with his grip. "Let's try the one on the right." He licked it gently at first, allowing his tongue to roll over my nipple. His deep, brown eyes locked onto mine before he bit down once more. This time, I felt a strange tickling sensation in my stomach and between my shoulder blades. My vision went black, and then white. I started seeing stars.

"AHHHH!" I yelped, ricocheting to life.

"That's right," he observed. "It was the right nipple. I was correct."

He flipped me once more onto my back, his hands meeting my neck once more. I felt the warm, gooey oil touch my skin once more, followed by his calloused, rough palms. They started rubbing at the back of my neck, and then gradually moving to my shoulders, squeezing back and forth playfully. He then glided over my arms, which sent a shiver up my spine. He squeezed them sharply, and he then started to knead my own hands. I felt curiously protected as I felt his large, firm palms envelope over my knuckles. He began to massage the skin that laid over my shoulder blades, and then slowly started to advance to the sides of my breasts. I squealed, immediately shushed by him as he traced a calloused finger over my spine.

"How are you so good at this," I breathed, in complete disbelief that his hands possessed the capability to work such magic against me. I was under his spell.

"Practice, my sweet," he responded, and elicited another moan from me by pinching the skin on my boobs. He was so gentle, almost kind with me as he proceeded with this foreplay. Skin was squeezed, hands were kneaded, flesh was pressed. His hands then proceeded to travel down onto the small of my back, working his way down toward my sultry hips. I wiggled my behind instinctively, adjusting myself as he went- adapting to his play. I was jolted like electricity once more as his palms squeezed the sides of my waist. He rubbed up and down, spreading the oil over my skin. It was the most intense feeling as his hands guided their way down onto my hips, kneading and pressing. The way he did everything- the way he knew exactly how I liked it- was absolutely exhilarating. His palms soon rested onto the top of my ass cheeks. They were plump and round, peachy like my skin tone, with a splash of carnation pink. They were still slightly tinged with scarlet from the spanking session earlier, but bubbly and effervescent nonetheless. I was surprised to feel his tongue rolling over the surface of my left cheek. I yelped in response to this action, the liquid in my stomach bubbling to life as he then proceeded to knead them with his rough hands.

"You like that?" he asked. His gruff voice was intoxicatingly sexy.

"Mmmph!" I moaned in response. "More, I want more, I want so much more!"

"As you wish," he replied simply, gripping my ass cheeks and then proceeding to kiss and suck. The suction noise after every single lick was so erotic to listen to. He sprinkled some more massage oil on top of my ass cheeks and continued to rub and squeeze and molest. I was surprised to see that he did not continue with the foreplay. Disappointed, I let out a girly sort of whine, and bit his blankets. He slapped my butt in order to surprise me, and then took a lock of hair, rubbing it into his hands as he lowered his lips to my ear.

"Stop being so impatient," he whispered huskily, and then planning a kiss onto my cheeks. "I am saving the best for last."

"Humph," I replied in response, pouting and turning away from him.

"What's wrong?" he asked, suddenly worried, those deep brown eyes abruptly overflowing with concern.

"Nothing," I responded, trying not to smile.

"Tell me what's wrong," he pressed stubbornly, now straddling my thighs with his own, strong protective arms like pillars shadowing over my delicate frame.

"I am not saying anything," I said.

"Mmm, I guess I will just have to get it out of you then," he replied with a smirk. As he lifted me up with his strong hands, my skirt naturally covered over my ass as he laid me gently onto a pillow, meeting his lips with mine. The kisses immediately became passionate and dirty, as his tongue intertwined with mine. I loved his kisses so much. I liked how his mouth fit perfectly over my own. I was his little petite angel, if only for a night. The types of make out sessions we had were not one dimensional- they were convoluted and intricate and filled with sparks. As I tried to wriggle away from him, his hips started to grind rhythmically with mine. Our tongues twisted and fought and swirled, quarreling against each other for dominance. He was a lot stronger than me- it was not my fault that I didn't lift weights and work out and command navies every single day. His strong biceps were more than thrice the size of my thin, feminine arms.

The bed creaked as we wrestled around and kissed. My toned, white stomach pressed against his rock hard abdomen. I traced a fingertip playfully over the rough, thick mountains, pausing between each crevice.

"So how often do you work out?" I asked in between each tongue.

"Every single day, why?" he countered playfully. "You are still avoiding my own question."

"How much can you bench?" I questioned again, still rubbing over his abs. He fortunately did not object, which was always pleasurable.

"Around 300 pounds, I would say," he replied enthusiastically.

"Ooo," I giggled. "That's more than twice of what I weigh."

"How much do you weigh?" he asked.

"Not telling," I responded.

"I am around 185 pounds," Gangplank said. "I am guessing you are around 120."

I did not say anything. We proceeded to make out for another ten or so minutes.

"Why were you upset earlier?"

I paused. "I wanted you to do stuff to my.. never mind."

"To your what?" he asked once more.

"M-my ass.." I replied timidly.

"You should have just said so, I did not know you were so keen on that," he countered, flipping me over roughly right when I began to drink in the make out session. His hands met my ass cheeks once more, rolling and squeezing and kneading and slapping. Once I was satisfied, he worked his way down to my thighs.

"They are so pretty," he commented. "Not too large, but not too thin." His hands rubbed over them, glazing them over with massage oil. He then worked his way to my calves. Once I started feeling relaxed, a spark began to ignite in my stomach as he started to massage my feet. I had no idea why they were so stimulated- it must have been the way his calloused palms scraped against them, or how his large, strong fingers poked in between my toes.

"Mmmm!" I moaned. "It tickles."

"I'll stop then," he replied, proceeding to put down my foot.

"Please don't," I countered, gasping into the bedspread.

"Fine," he responded, kneading my feet with the utmost care. I heaved a sigh of relief, and smiled into the cushion beneath me as I enjoyed the way his hands massaged my feet. Right when I started to become accustomed to the slow pace, he pulled me upwards, almost roughly.

"Let's stop with all this lovey-dovey bullshit," he said roughly. "I am making you change into this." He revealed a naughty piece of lingerie, paired with a sheer corset and lacy, transparent push-up bra. A bottomless thong was also paired with the outfit, in addition to suggestive fishnet stockings and ruby red high heels. I hated how he dressed me up like a doll.

"Put your hands behind your back," he commanded. Suddenly struck with fear, I immediately did as I was told, eyeing the poker stick in the corner of the bedchamber nervously. My skin was still glistening with a combination of sweat, saliva, and massage oil. He removed the schoolgirl uniform I was squeezed into earlier, and then fit the tight, lacy bra over my enormous boobs.

"Can barely hold them in," he murmured to himself, cupping them with his hands and bouncing them. I hated how he did that, and growled in response.

"Feisty," he chuckled. "They are so huge.." They really were. Large, white, but round and very elegant. They were like two circular bubbles, embellished with an innocent, blush nipple. My breasts spilled over the petite corset as he tied it all up, the fabric squeezing my curvy hourglass figure. I felt slightly embarrassed as he fit the bottomless thong over my pussy, the juices spilling over my inner thigh. He then fit on the fishnet stockings, as I became more wet as the gauzy material bit over my sensitive skin. With the high heels as the finishing touch, he then started to carry me onto the bed, pushing me over the sheets and spreading my legs open. I moaned as the cold air bit my vagina like ice.

I shook my head violently and sat upwards. "I don't know about this, Gangplank.." I whimpered nervously. "I just don't know.." He sighed with annoyance, allowing me to rest my head against his exposed chest, which was so muscular and nice-looking. I just wanted to sit on his lap and caress his intensely trained body. He bit my ear, surprising me, and pushed me against the bed.

"Spread 'em," he said. I did exactly as I was told. I closed my eyes tightly, hands still cuffed tightly behind my back. Electricity crept up my back as he breathed a puff of air over my pussy lips. His tongue met the outer labia and proceeded to flick at the skin folds.

"Mmph!" I squealed. "So good.."

"I knew you would come around," he responded, asserting his dominance once more by clamping his hands over my inner thighs and pulling my pussy closer toward him. He breathed in my heavenly scent, as his mouth returned once more to my vagina. His tongue felt amazing as it started to move toward my inner labia. I started moaning in a high-pitched voice as his tongue began to flick at a faster rate, kissing and sucking and nibbling. I gripped the blankets beneath me for dear life as the oral sex intensified.

"Ah, ah, ah, ah, ah!" I yelped, biting my lips, my eyes blurring. Just as I was instinctively wriggling away, he pulled me closer toward him with such force. He drank in my juices, sucking and squeezing and licking. It was so good. I felt so good. It was absolutely amazing. I started to feel so much sensation building in my lower stomach and then creeping toward my nether region. Something about the way his mouth moved lit me on fire.

"More more more!" I groaned, jumping as his stubbly chin tickled my soft parts. He cleaned up any spare lines of cum with his tongue and proceeded to torture me with his mouth. He suddenly paused, breathing another puff of air onto my pussy and allowing air to touch it. I clenched at this action, my entire body tightening with anticipation. He met my pussy once more with his tongue after what seemed like an eternity, and sucked and licked me to oblivion.

"You are so wet," he commented. Just before I could reply, he fit one dry finger into my hole. I took a breath in, feeling the skin of his hands scrape my insides.

"AHHHHH!" I yelped, biting my lips and closing my eyes, breasts bouncing every time his finger drew in and out of me. He then decided to insert a second digit, and then a third, and then a fourth.

"Mmm, oh yes, oh yes, oh YES!" I responded, saliva trickling from the corners of my mouth and onto the sheets.

"You naughty girl," Gangplank snapped. "Miss Fortune, you dirty little whore."

"Give it to me," I screamed. He propped me up against the frame of the bed and inserted a digit in between my lips. I grabbed his large finger with my delicate hands, and licked it playfully with my tongue. I made sure to clean everything up, leaving no trace whatsoever behind. My pussy was still wet, and throbbing with delight. The thong was entirely soaked through.

"Mmmm," I moaned, cleaning the finger with my tongue.

"You sexy little slut," he whispered, tucking a piece of hair behind my ear as I sucked. "You little cock whore. All mine."

He proceeded to remove his top, allowing my eyes to glaze over his perfect, muscular torso. He then unbuckled his belt, throwing his trousers to the side of the bed. Removing his tight boxers, he exposed his enormous length. It was absolutely huge. I covered my mouth, in absolute shock.

"Oh my god," I whispered to myself. "It's so big."

"Don't pretend you've never seen it before, Fortune," Gangplank smirked, rubbing it with his hands.

"Yeah, but it still surprises me every time," I replied. "Like.. oh my gosh."

I reached out to stroke it, the tip already glistening with precum. I snorted. Figures. It takes more than this to get Gangplank going. After massaging the penis for several minutes, I fit my mouth over the monster, bobbing my head up and down, and staring at him in the eyes. He placed his fingers into my hair, the ruby tresses pouring through his hands. Every time my mouth released from the giant cock, it made a satisfactory suction noise. Never in a million years would I have imagined myself giving the obnoxious Gangplank the blow job of his life. But I could tell that I sort of owed it to him, given the oral and the massage, and the make out sessions. I placed both hands on top of the fleshy rod, and started to deep throat. I knew he liked that the most. I flicked my tongue over the enormous length and released, allowing a line of saliva to connect to the tip of the cock and my lips. I then slipped my tongue underneath it, eliciting a roar from Gangplank. The cock started to touch my gag gland. I started to choke on it, barely able to breath. I continued to move my head up and down in the same rhythmic motion. It was only fair.

"Get up," he commanded, having enough. I nodded in response as he pushed me against a wall, my back faced toward him and my ass in a vulnerable state. Relieved that it was lubricated, I sucked in a breath as he pushed his cock in between my butt cheeks. This was different. So very different. Anal. Huh. I screamed, clawing at the surface before me. He hugged my waist against his abdomen, ramming into me repeatedly. I loved how complete I felt whenever we were having sex. I felt so free and desirable and sexy and young and wanted. Being with Gangplank just felt so perfect and right. We proceeded to bang around for a good thirty minutes or so, my hands still handcuffed behind my back and Gangplank ramming into me like a well oiled machine. He then started to push into my vagina, banging and ramming and pushing, ignoring all of my pleas to stop. My vision was blurring, drool dripping from my lips and onto the floor, as the sex continued for several hours straight. I was tired and worn out, completely ready to finish. Gangplank was still unsatisfied.

"Wrap your thighs around my waist," he commanded. I did exactly so, as he fit his gigantic cock into my pussy and bounced me up and down.

"Mmm, ahhh, agh," I moaned, rested my chin onto his neck. This continued for another twenty minutes or so.

"Still not good enough.." Gangplank muttered. He placed me onto my hands and knees, ass in the air, and rammed his cock into my asshole.

"Ahhh.." I squealed, eyes glazing over. My throat was sore, my legs went limp, and my chest heaved up and down as Gangplank rammed into my continuously with frustration.

I started to feel a hot buildup in my stomach, slowly clambering upward into my throat. I heard Gangplank begin to groan as we both orgasmed simultaneously. The night ended as we collapsed into bed together, both reaching climax and now settling down. I removed the itchy lingerie and wrapped my body around his muscular frame. I felt tiredness, exhaustion, and the drunkenness from the bar earlier begin to take over my senses.

"Why do we always end up doing this, Gangplank," I moaned. "It's honestly so.. tiring."

"I may be able to resist you, Sarah Fortune," Gangplank murmured. "But you obviously can't resist me." He planted a kiss onto my forehead as I nestled myself into his strong, protective arms.

"Huh.." I whispered, entertaining the thought, breathing in his lovely scent. "Okay.."

The next morning I awoke, he was gone. I felt somewhat refreshed, smacking my lips and stretching my arms behind my head. I started to miss him already. I felt the place where he slept beside me yesterday night. It was not warm. I could have kicked myself. Stupid, stupid stupid. I just slept with Gangplank. How many times was this again? This would spread around all over Bilgewater I just know it. Miss Fortune, the cheap little prostitute, sleeping around. Dumb, dumb, dumb! I buried my face into my hands. What have I done. I pushed my red hair out of my eyes and tightened my legs, releasing some tension from last night. I looked around the room. The bedchamber was a mess. The chair where I gave him the lap dance was toppled over, clothes strewn all over the floor. The curtains where I gripped onto for dear life as he banged into my has fallen over, and the area on the wall where I clawed as he pushed me against it was peeling ever so slightly. The covers on the bed were pushed onto the ground, and several pillows were also spread across the room. His hat was missing as well. I decided to shower and get dressed. Might as well after a night of banging around. I stepped into a shower case in a separate portion of the regal room, and felt the warm water trickle over my body, scrubbing myself with soap and some hair products.

"What the fuck was that?" I asked myself. "How could I be so easy.. damn that bastard." I turned the water off and decided to put on some of Gangplank's spare clothes. I found a clean, beige blouse and fit it over my torso. It seemed somewhat gender neutral, and suited me quite nicely. I slipped on the mini skirt from yesterday night and the ruby heels he made me wear. Those were actually quite appealing. We had similar tastes. I stepped my way out of the bedroom and maneuvered my way downstairs. I rubbed the sleep out of my eyes, and was surprised to find Gangplank sitting in the living room, smoking a cigar and taking a swig of vodka.

"Morning, sexy," I greeted sultrily.

He looked up from his concentration and smirked. "Hey."

"Mmm," I moaned as I stepped toward him, wrapping my arms around his neck. "So about last night.."

"Haha, no," he laughed, pushing me aside. "What happened last night stays in this house."

"Hmmm," I licked my lips, trying to seduce him by kissing his neck. It failed miserably, to my dismay.

"Just get out.." he replied, pushing me away. My mood was immediately dampened as I pouted.

"But why.." I whimpered.

"Get your clothes and your shit," Gangplank murmured roughly. "You don't have to be my sex slave for a month, it's fine. Just take your belongings and leave."

"But what if I want to be," I replied, still standing behind his armchair.

"I don't," he responded, lighting another cigar.

"But why not.." I whined.

"People talk, and I don't need that shit," Gangplank said. He was in a bad mood, I knew it. "I packed your stuff in some spare luggage, and your clothes are in there too."

I pouted, stealing his hat and placing it on top of my head. "But I like you," I murmured quietly, taking the canister of vodka and sipping.

Gangplank shrugged. "I'm sorry."

I whimpered again, sitting on his lap, locking my sexy, irresistible eyes into his own. "Pretty please?" I asked.

"No," Gangplank chuckled. "So persistent." He didn't lay a finger on me, as I moved my hands over his face and hair.

"I want you to fuck me, use me, suck me, lick me.. destroy me.." I whispered, licking his ear and releasing a seductive moan.

"Sarah.." Gangplank stood up. "Just go."

He picked up a suitcase that stood next to the coffee table in his luxurious lounge and grabbed my arm, leading me to the door. I gripped onto his sleeve for dear life, refusing to move. He used this opportunity to remove his hat from the top of my head and placing it onto his own. He opened the door, gesturing for me to walk out of the threshold. What a douchebag. I grabbed my suitcase from his hands, standing before him. He towered a feet above me, his muscular frame dwarfing mine. I was now at the entrance, about to leave. Probably won't see him again for another few months.

"I'll miss you.." I squealed, in a high-pitched voice.

I wrapped my arms around his waist and buried my face into his chest. He reciprocated by embracing me, not too tightly, of course.

"I'm sorry," he said once more. "But I just can't. And if you look at it, I am doing you a favor."

"Okay," I replied, wiping some tears from my eyes.

"Are you crying?"

"N-no."

He stood there for a second. He then placed his hand on top of my head, patting it affectionately.

"You'll see me again, I promise," he assured. He then planted a kiss boldly onto my cheek. I suddenly lit up.

"Yeah.. okay…" I responded. I then ran off into the distance, probably to catch a boat at the harbor somewhere, leaving him and the night before behind.


End file.
